Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
AmericInn by Wyndham Beaver Dam

AmericInn by Wyndham Beaver Dam

2.5 out of 5
Price was $455, price is now $386 per person
$386
per person
Dec 11 - Dec 14
found 12 hours ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
This hotel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. There's a bar/lounge on site, and laundry facilities and free newspapers are also provided.
Holiday Inn Express & Suites Beaver Dam by IHG

Holiday Inn Express & Suites Beaver Dam by IHG

2.5 out of 5
Price was $472, price is now $428 per person
$428
per person
Dec 11 - Dec 14
found 12 hours ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
Price was $415, price is now $398 per person
$398
per person
Dec 11 - Dec 14
found 12 hours ago
Roundtrip non-stop flight included
New York (NYC) to Madison (MSN)
This hotel features an indoor pool, a hot tub, and a restaurant. Enjoy the gym and free perks like continental breakfast and free self parking. Free WiFi in public areas is provided and the front desk is staffed around-the-clock.

Top Windsor hotels deals

Days Inn by Wyndham Madison NE/Windsor

Days Inn by Wyndham Madison NE/Windsor

2 out of 5
6311 Rostad Dr, I-90/94 and Hwy 19, Windsor, WI
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $66 total per night
$66 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.
Pool
Hot Tub
Super 8 by Wyndham Windsor/Madison North

Super 8 by Wyndham Windsor/Madison North

2 out of 5
4506 Lake Circle, Windsor, WI
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $76 total per night
$76 total
Nov 9 - Nov 10
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Pet friendly
Parking included
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $161 total per night
$161 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Hot Tub
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr, Madison, WI
Free Cancellation
Reserve now, pay when you stay
$66 nightly
The price is $77 total per night
$77 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center

3 out of 5
5217 E Terrace Dr, Madison, WI
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $87 total per night
$87 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like continental breakfast and free self parking. A 24-hour business center, a lobby fireplace, and a communal living room are also on offer.
Pool
Hot Tub
Best Western West Towne Suites

Best Western West Towne Suites

2.5 out of 5
650 Grand Canyon Dr, Madison, WI
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $93 total per night
$93 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Breakfast included
Pet friendly
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Cool street art in Madison, Wisconsin

University of Wisconsin-Madison

Enjoy the collegiate vibe around University of Wisconsin-Madison, a top college in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Capitol Building

Capitol Square

You can find out about the history of Madison with a visit to Capitol Square. Visit the area's shops, or simply enjoy its restaurants.

Capitol Square
Great place to check out the sunset and hang out with friends and family!

Monona Terrace Community and Convention Center

Learn about the events happening at Monona Terrace Community and Convention Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Monona Terrace Community and Convention Center

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity provides flight and hotel vacation packages starting from just $386. With such huge savings, you'll be exploring all of Windsor in a flash.
How long should my Windsor vacation be?
Many travelers choose to spend about 2 nights in Windsor, but it's your call. If you want to venture out and explore all the exciting things this location has waiting for you, why not hang around another night or two?
Where can I get the best vacation package deals for Windsor?
It's difficult to beat Travelocity when it comes to finding your Windsor package deal. There are at least 400 air carriers and 1,000,000 properties worldwide to select from. Reserve your trip now and get ready to cross another exciting place off your must-visit list.
Why should I purchase my Windsor vacation package via Travelocity?
By booking your hotel, flights, activities and car rental all in the one place, you'll save both time and money. All our bookings come with round-the-clock customer support, and you'll know that you'll always score the lowest price possible with our Price Match Guarantee. So, what are you waiting for? Book the vacation of your dreams today and get packing!
Can I save on my Windsor car rental if I combine it with a hotel or flight?
Certainly — bundle your car, flight and hotel into a Windsor vacation package and you'll save a ton. With so much to uncover in the Windsor area, that set of wheels will make exploring a joy. Once you've slid into the driver's seat, get out on the wide open road and cruise toward Wrigley Field, a top sight around 120 mi from Windsor.
Which airport is best for Windsor?
The most convenient airport for Windsor is Dane County Regional Airport (MSN). You'll find it 6 mi north of the city center.
What is there to do in Windsor?
Mousehouse Cheesehaus should be on your travel schedule. After you've checked off this top attraction, simply stroll the streets of Windsor and get a feel for what makes this fantastic destination tick.

Photos of local treasures

Browse Windsor vacation photos for more inspiration

Photo by Joel Holland
Photo by Joel Holland